Triethylamine → [4-(3,4-Dichloro-phenoxy)-[1,4']bipiperidinyl-1'-yl]-(2-methanesulfonyl-phenyl)-methanone

HRID 349743ノート

反応式

HRID 349743 の反応式
C(Cl)(=O)C(Cl)=O.[CH3:7][S:8]([C:11]1[CH:19]=[CH:18][CH:17]=[CH:16][C:12]=1[C:13]([OH:15])=O)(=[O:10])=[O:9].[Cl:20][C:21]1[CH:22]=[C:23]([CH:37]=[CH:38][C:39]=1[Cl:40])[O:24][CH:25]1[CH2:30][CH2:29][N:28]([CH:31]2[CH2:36][CH2:35][NH:34][CH2:33][CH2:32]2)[CH2:27][CH2:26]1.C(N(CC)CC)C>C(Cl)Cl.CN(C=O)C>[Cl:20][C:21]1[CH:22]=[C:23]([CH:37]=[CH:38][C:39]=1[Cl:40])[O:24][CH:25]1[CH2:26][CH2:27][N:28]([CH:31]2[CH2:32][CH2:33][N:34]([C:13]([C:12]3[CH:16]=[CH:17][CH:18]=[CH:19][C:11]=3[S:8]([CH3:7])(=[O:9])=[O:10])=[O:15])[CH2:35][CH2:36]2)[CH2:29][CH2:30]1

参加物

7

反応物 4

HCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 2843422-Methanesulfonylbenzoic acidHCID 223974344-(3,4-Dichloro-phenoxy)-[1,4']bipiperidine

生成物 1

HCID 22397458[4-(3,4-Dichloro-phenoxy)-[1,4']bipiperidinyl-1'-yl]-(2-methanesulfonyl-phenyl)-methanone収率 76.8%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 6344Dichloromethane溶媒4 回

実験手順

Oxalyl chloride (55 ml, 0.63 mol) was added dropwise over 10 minutes to a stirred suspension of 2-methanesulfonyl-benzoic acid (7.1 g, 0.036) in DCM (550 ml) containing DMF (0.5 ml). The solution was then stirred for 2 hours at room temperature. The solution was then evaporated to give a solid that was redissolved in dichloromethane and again evaporated to give a yellow solid. The solid acid chloride was dissolved in DCM (275 ml) and was added over 10 minutes to a stirred solution of the product of Step 3 (11.0 g, 0.033 mol) and triethylamine (15.4 ml, 0.11 mol) in dichloromethane (125 ml). The resultant solution was stirred at room temperature for 16 hours. The solution was then washed with water (500 ml), 1M aq NaOH (500 ml) and water (2×500 ml). The organic phase was dried (MgSO4), filterered and the solvent removed to give a pale yellow foam. The foam was triturated with diethyl ether to give the title compound (12.96 g, 76%).

後処理

  1. customThe solution was then evaporated
  2. customto give a solid
  3. customagain evaporated
  4. customto give a yellow solid
  5. washThe solution was then washed with water (500 ml), 1M aq NaOH (500 ml) and water (2×500 ml)
  6. dry with materialThe organic phase was dried (MgSO4)
  7. customthe solvent removed
  8. customto give a pale yellow foam
  9. customThe foam was triturated with diethyl ether

出典と根拠

ORDレコード
ord-3c0d8bcb0d2e4b9db065c0414a32c98b
出典データセット
uspto-grants-2007_02
特許番号
US07179922B2

反応ノート

読み込み中…